{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T17:01:02Z","timestamp":1790787662961,"version":"4.1.0"},"reference-count":32,"publisher":"Wiley","issue":"10","license":[{"start":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T00:00:00Z","timestamp":1790726400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"},{"start":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T00:00:00Z","timestamp":1790726400000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/doi.wiley.com\/10.1002\/tdm_license_1.1"}],"funder":[{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["22167012"],"award-info":[{"award-number":["22167012"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry &amp;amp; Biodiversity"],"published-print":{"date-parts":[[2026,10]]},"abstract":"<jats:title>ABSTRACT<\/jats:title>\n                  <jats:p>\n                    Shimobashiric acid C (SBA\u2010C) shows excellent hyaluronidase inhibition but its natural isolation yield is only 0.0092 %. We report its first synthesis via a convergent seven\u2010step route from caffeic and rosmarinic acids in 35% overall yield. Direct protection of\n                    <jats:italic>D<\/jats:italic>\n                    \u2010Danshensu (\n                    <jats:italic>D<\/jats:italic>\n                    \u2010DSS) with 2,2\u2010dimethoxypropane gave an isochroman; the desired acetonide\u2010protected\n                    <jats:italic>D<\/jats:italic>\n                    \u2010DSS building block was instead prepared from methyl rosmarinate via bis\u2010acetonide formation followed by methanolysis. Acetonide\u2010protected caffeic acid was synthesized and crystallized in a\n                    <jats:italic>P<\/jats:italic>\n                    \u20101 lattice, where linear hydrogen\u2010bonded caffeic acid pairs pack with adjacent alkenyl bonds aligned at 3.919\u00a0\u00c5 for head\u2010to\u2010tail solid\u2010state [2+2] photodimerization. Irradiation at 365\u00a0nm gave the acetonide\u2010protected\n                    <jats:italic>\u03b1<\/jats:italic>\n                    \u2010truxillic acid building block. The two blocks were condensed via Steglich esterification to give acetonide\u2010protected SBA\u2010C methyl ester. Selective deprotection of the acetonide groups was achieved with 55% trifluoroacetic acid in the presence of trace water in nearly quantitative yields. This mild deprotection caused no noticeable side reactions and may be applied to synthesis of other\n                    <jats:italic>D<\/jats:italic>\n                    \u2010DSS\u2010containing phenolic acids, such as salvianolic acids.\n                  <\/jats:p>","DOI":"10.1002\/cbdv.71738","type":"journal-article","created":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T16:07:24Z","timestamp":1790784444000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":0,"title":["First Synthesis of Shimobashiric Acid C With Acetonide as the Catechol Protecting Group"],"prefix":"10.1002","volume":"23","author":[{"ORCID":"https:\/\/orcid.org\/0009-0008-6914-6557","authenticated-orcid":false,"given":"Ruwen","family":"Li","sequence":"first","affiliation":[{"name":"School of Pharmaceutical Sciences Hainan University  Haikou Hainan Province P.R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhe","family":"Zhang","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences Hainan University  Haikou Hainan Province P.R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pengshu","family":"Xu","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences Hainan University  Haikou Hainan Province P.R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lin","family":"Zhou","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences Hainan University  Haikou Hainan Province P.R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lei","family":"Chen","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences Hainan University  Haikou Hainan Province P.R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhongqiang","family":"Liu","sequence":"additional","affiliation":[{"name":"School of Pharmaceutical Sciences Hainan University  Haikou Hainan Province P.R. China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2026,9,30]]},"reference":[{"key":"e_1_2_9_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.biomac.2c00207"},{"key":"e_1_2_9_3_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules28052084"},{"key":"e_1_2_9_4_1","doi-asserted-by":"publisher","DOI":"10.3390\/foods14081362"},{"key":"e_1_2_9_5_1","doi-asserted-by":"publisher","DOI":"10.1248\/cpb.60.121"},{"key":"e_1_2_9_6_1","doi-asserted-by":"publisher","DOI":"10.3390\/medicines6010037"},{"key":"e_1_2_9_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/S2707-3688(23)00039-0"},{"key":"e_1_2_9_8_1","doi-asserted-by":"publisher","DOI":"10.3390\/molecules23092277"},{"key":"e_1_2_9_9_1","first-page":"223","article-title":"Anti\u2010Apoptotic Effects and Mechanisms of Salvianolic Acid A on Cardiomyocytes in Ischemia\u2010Reperfusion Injury","volume":"34","author":"Qian W.","year":"2019","journal-title":"Histology and Histopathology"},{"key":"e_1_2_9_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bcp.2017.04.007"},{"key":"e_1_2_9_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(98)01896-6"},{"key":"e_1_2_9_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tet.2016.05.070"},{"key":"e_1_2_9_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja052680h"},{"key":"e_1_2_9_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2008.07.052"},{"key":"e_1_2_9_15_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41467-025-58444-8"},{"key":"e_1_2_9_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/jacs.4c16252"},{"key":"e_1_2_9_17_1","doi-asserted-by":"publisher","DOI":"10.1039\/D5NP00023H"},{"key":"e_1_2_9_18_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2005-918502"},{"key":"e_1_2_9_19_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0CE01403F"},{"key":"e_1_2_9_20_1","doi-asserted-by":"publisher","DOI":"10.1351\/pac197127040647"},{"key":"e_1_2_9_21_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.chempr.2020.11.010"},{"key":"e_1_2_9_22_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201100271"},{"key":"e_1_2_9_23_1","first-page":"39","article-title":"Chirale 2\u2010Benzopyran\u20103\u2010Carbons\u00e4ure\u2010Derivate Durch Oxa\u2010Pictet\u2010Spengler\u2010Reaktion Von (S)\u20103\u2010Phenylmilchs\u00e4ure\u2010Derivaten","volume":"1992","author":"W\u00fcnsch B.","year":"1992","journal-title":"European Journal of Organic Chemistry"},{"key":"e_1_2_9_24_1","unstructured":"P. B.Messersmith B. H.Hu andZ.Liu Method of Synthesizing Acetonide\u2010Protected Catechol\u2010Containing Compounds and Intermediates Produced Therein US8227628B2(2012)."},{"key":"e_1_2_9_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2024.155150"},{"key":"e_1_2_9_26_1","first-page":"149","article-title":"Simple and Efficient Synthesis of Acetonide\u2010Protected and N\u2010Protected L\u2010Dopa Derivatives","volume":"45","author":"Xu P.","year":"2023","journal-title":"Chemical Reagents"},{"key":"e_1_2_9_27_1","unstructured":"Z.Liu X.Zhang B.Hu et\u00a0al. Synthesis method and application of intermediate of DOPA oligopeptide composition and preparation CN111153885A(2020)."},{"key":"e_1_2_9_28_1","first-page":"232","article-title":"Identification of Catechols and Their Protecting Groups Using Color Reactions","volume":"14","author":"Meng M.","year":"2024","journal-title":"Journal of Tropical Biology"},{"key":"e_1_2_9_29_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202208994"},{"key":"e_1_2_9_30_1","doi-asserted-by":"publisher","DOI":"10.1039\/p29840000181"},{"key":"e_1_2_9_31_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00112a007"},{"key":"e_1_2_9_32_1","doi-asserted-by":"publisher","DOI":"10.1080\/10587259808044274"},{"key":"e_1_2_9_33_1","doi-asserted-by":"publisher","DOI":"10.1039\/c6pp00201c"}],"container-title":["Chemistry &amp; Biodiversity"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbdv.71738","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cbdv.71738","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbdv.71738","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,30]],"date-time":"2026-09-30T16:07:27Z","timestamp":1790784447000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/cbdv.71738"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,30]]},"references-count":32,"journal-issue":{"issue":"10","published-print":{"date-parts":[[2026,10]]}},"alternative-id":["10.1002\/cbdv.71738"],"URL":"https:\/\/doi.org\/10.1002\/cbdv.71738","archive":["Portico"],"relation":{},"ISSN":["1612-1872","1612-1880"],"issn-type":[{"value":"1612-1872","type":"print"},{"value":"1612-1880","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,30]]},"assertion":[{"value":"2025-11-26","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-09-08","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2026-09-30","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e71738"}}